Shelter Island Vacations
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Where to stay in Shelter Island
Silver Beach
While Silver Beach might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Sunset Beach and Crescent Beach.
Find the Best Shelter Island Vacation Packages
Shelter Island Beach Vacation
There's nothing like a Shelter Island vacation to give you a little extra bounce in your step. The sound of rolling surf and the smell of clean ocean air are sure to refresh your mind, body and soul. To be close to the town center on your trip to Shelter Island, find a hotel around Wades Beach (2 kilometers away). If you're planning to stay for a bit, look into our Shelter Island packages. Not only can you save some cash, you'll also have other amazing beaches near you to explore, like Shell Beach and Menhadden Lane Beach.
Shelter Island Hotel Deals
Gurney's Montauk Resort & Seawater Spa
Our family of four stayed for 3 nights in a two bedroom suite with ocean views. We booked it last minute for spring break. Overall, we had an amazing time and enjoyed our stay despite the cold temps. The room was clean. I saw no obvious signs of aging of furniture, fittings and walls - a huge plus ...
Reviewed on Apr 14, 2026
Montauk Manor
We stayed in a 1 bedroom deluxe loft. Only downfall is how much and how loud the noise travels throughout the unit. Next stay will definitely be a 2 bedroom.
Reviewed on Apr 17, 2026
Sound View Greenport
The check-in staff were friendly and helpful, finding us a different room when ours wasn’t available. The breakfast was significantly better than a simple continental, offering a variety of items. It is a sprawling complex on the LI sound, with nice views from our room and the dining areas. The restaurant, ...
Reviewed on Apr 17, 2026
Discover the most popular places to visit in Shelter Island
Havens House
You can spend an afternoon browsing the exhibits at Havens House during your trip to Shelter Island. Stroll along the area's beaches or simply enjoy its wineries.
